Jane Powell in The Girl Most Likely, 1958

Dodie dreams of marrying a millionaire so that she can live ‘the life’. Buzz, her boyfriend, however is not rich as he is a salesman for a housing development. He proposes and Dodie accepts. Dodie next meets Pete, who she thinks is rich, but she soon finds out that he is just a boat mechanic. They have fun on their date and Pete proposes and Dodie accepts. Then Dodie meets Neil Patterson who is rich. They go to Mexico on his yacht and have fun on their date. Neil proposes and Dodie accepts. Now she has to choose.